Chicago Is An Elite Bachelor Party Destination In America And Here Is Your Definitive Guide.

This blog is LONG overdue. 

White Sox Dave and I get absolutely bombarded weekly with tweets, DMs, carrier pigeons, you name it, all asking the same damn questions- "Hey, I'm visiting Chicago soon, where do I eat? Where do I drink? Where do I sleep?"

Instead of continuously repeating ourselves, I figured the most entertaining and comprehensive way to answer everyone's questions would be to frame it around a bachelor party weekend. But don't worry, there's a little something here for everyone, whether you're celebrating impending nuptials, trying to tie one on with the boys, or just visiting the city for the weekend. You can find something useful in here, I promise. 

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So, here’s your definitive, foolproof guide to enjoying Chicago the way God intended. Even if nobody you know is tying the knot soon, use this anyway. It's summer, the sun is shining, and Chicago is calling your name louder than the last round of shots at 4 AM. (Yah, Chicago bars go til 4 AM. And 5AM on Saturdays.)

If Vegas is the undefeated heavyweight champ of bachelor party destinations and Nashville is the flashy new contender that’s knocking guys out left and right, Chicago is the guy in the division who doesn’t talk much, but if you’ve been in the game long enough, you know he’s a problem. Summer here is a different breed. we've got perfect weather, endless sports, world-class restaurants, and a bar scene that goes pound-for-pound with anywhere in the country.

This isn’t Yelp fluff or some corny travel blog. This is from someone who has lived here, partied here, eaten here, blacked out here, and woken up here wondering how he ended up holding a gyro from Mr. Greek in a park at 5 AM.

Chicago summers are legendary for one simple reason: we suffer through six months of frozen hell just to spend three months day-drinking on patios, beaches, and boats like the degenerates we are. The second May hits, this city explodes into something you can’t really explain until you see it. Patios open overnight. The beaches fill up. Lake Michiagn gets slammed with boats. Girls in sundresses seem to materialize out of thin air. Every single person is suddenly day-drinking like it’s their full-time job. The city’s population triples, the sun’s out until damn near 9 PM.

Chicago summers are unbeatable. We have an incredible city situated right on the stunning shores of Lake Michigan, lined with beaches and parks that stretch for miles. 

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This city is an absolute grindhouse from November to April. It’s dark, windy, icy, and the locals carry around a thousand-yard stare like they’ve been in the trenches. So when the first sign of sunshine arrives, patios open, aforementioned sundresses make their triumphant return (sorry, but I'm a huge fan of them), and Chicagoans immediately shift gears into professional day-drinking mode. 

Unlike New York, Boston, or Philly, where summer means everyone bails for the beach, Chicago is the opposite. Here, summer is the beach trip. People flood in from every surrounding state. The population feels like it triples overnight. And that energy- that “holy shit, we made it” energy, is exactly what you want for a bachelor party.

With two major airports, O'Hare and Midway, you can get here directly from virtually any major city in the U.S., a huge convenience when organizing a big group.

Plus two we have two baseball teams, because misery loves company and God loves balance. That means baseball basically every single day. 

Every weekend is packed with neighborhood street fests featuring beer tents, live music, and drunk locals who swear they went to high school with Kanye.

And then there's our restaurant scene, widely considered the best in the nation, plus bars that stay open until 4 AM on Fridays and 5 AM on Saturdays. 

It's not Las Vegas, but Chicago stacks up pretty well against anybody for bachelor party city destinations in the summertime. 

Allow me to make my case- 

GETTING HERE 

First off, it's insanely convenient. 

Like I mentioned, with two airports, and being centrally located, Chicago travel is incredibly easy compared to getting into a smaller airport or having to fly from one side of the country to the other. I'm personally a Midway guy because flying Southwest is easy, straightforward, and most of all avoids the heavy traffic near O'Hare. Flying into O’Hare is like willingly booking a dentist appointment at 4 PM on a Friday. Painful and unnecessary. Midway is Southwest country, easy in, easy out, and the cab line doesn’t look like a refugee camp. If you love waiting in traffic or feeling miserable, by all means, choose O’Hare.

O'Hare, though busier and more congested, offers more direct flights and is great if you don’t mind taking the Blue Line into the city or flying at off-peak times. But if you get stuck in that traffic on 90/94 you will regret it for hours while you're stuck in standstill traffic. If you do get stuck flying into O’Hare, please for the love of God take the Blue Line train straight downtown. It’s the 16th stop, so you can zone out, pass out, or crush a road beer (allegedly) without worrying about missing it. Ride it during the day, though, because the late-night Blue Line is its own episode of Law & Order.

PRO MOVE = O’Hare is where joy goes to die. It’s a sprawling hellscape of delays, screaming kids, and TSA lines that feel like a hostage situation. Midway is smaller, faster, Southwest-heavy, and 20 minutes to downtown in an Uber if traffic’s decent. You land, you’re drinking a beer in your hotel before your buddies at O’Hare have even reached baggage claim.

WHERE TO STAY

As for where to stay, unfortunately, Chicago has cracked down heavily on Airbnbs. Your safest bet is a hotel, and thankfully, there are countless options at every price point.

If you want to roll right out of bed and into the party, stay at Hotel Zachary in Wrigleyville. You’re literally across the street from Wrigley Field. You can watch drunk Cubs fans spill into the streets from your window and be part of it in less than 30 seconds.

If you’re going for hipster-cred and rooftop views, The Robey in Wicker Park is your move. It’s got that “we’re staying here because my buddy who used to date a girl in a band told me about it” vibe.

Hotel Lincoln in Lincoln Park is another solid option, especially if you plan to day-drink on their rooftop bar, J Parker, which gives you some of the best skyline views in the city.

You’ve got your downtown power moves like the LondonHouse, which comes with a rooftop bar so photogenic it should charge a cover just for walking in. The Pendry’s got that sleek, modern, “we’re pretending to be classy before getting blackout” vibe. Or you can hit The Godfrey, which is basically a nightclub with hotel rooms attached.

If you’re trying to stay a little more low-key but still in the action, there’s the Virgin Hotel, which somehow manages to feel cool without trying too hard. And if you’re a “we want a pool” group, you’re looking at The Hoxton in Fulton Market — perfect for when the hangover sets in and you want to bake in the sun like a rotisserie chicken while the rooftop servers keep the Bloody Marys coming.

Airbnb is also in play, but here’s the thing: in Chicago, you’re not getting some massive Miami-style bachelor mansion. You’re getting a converted industrial loft or a classic Chicago three-flat in Wicker Park. The upside? You can walk to bars, avoid $30 Ubers, and really soak up that neighborhood feel. The downside? One bathroom for ten dudes is a war crime.

And if you’re playing it safe, downtown has every chain hotel you can think of, but book early, especially if your trip overlaps with Lollapalooza or any major festival weekend.

PRO MOVE = Use whoever in your group has the most Bonvoy or Hilton points and nab a suite at one of the Westins, or The St. Regis, or nicer Hilton properties downtown along with a few rooms on the same floor. Put the groom and a few of his buddies in the suite and the guys who snore in their own room(s). Use the suite as a home base and meeting point. If you have somebody in your group who hit it big on Bitcoin last year, have him flex and take care of everybody at The Peninsula, The Langham, or Trump if they aren't anti Trump as those are the three nicest spots you'll find downtown.

Also: Chicago’s neighborhoods are compact. This isn't like Houston where everything's an hour apart. A ten-minute Uber swing can completely change your night. Plant yourself in one area per session and let the city come to you.

WHERE TO EAT (From Hangover Triage to the Gentleman Dinner)

Your diet ends here. Do not plan to visit Chicago and "eat clean", or even eat healthy. It's impossible. 

Chicago’s the best restaurant city in the country because we do everything well. You can run the full spectrum: casual and cheap with the boys two nights, splurge for the “gentleman dinner” one night. And yes, seafood exists here; no, it’s not why you flew to a landlocked state (asterisk: Joe’s Stone Crab is the rare exception- same sauce-and-crack ritual you know from Miami, and hilariously, the fried chicken is world-famous for good reason).

Breakfast (Build the Base)

Breakfast is the most important meal, especially if last night involved questionable decisions.

Breakfast in Chicago is secretly run by Greek families, and Greeks don’t miss. Yolk is everywhere- skillets, omelets, pancakes the size of steering wheels. Meli Café is lights-out for hangovers. Lou Mitchell’s near Union Station is a rite of passage, bottomless coffee, free donut holes at the door, servers who move like they’re calling audibles at the line. You’ll intend to “eat light,” then find yourself elbows-deep in a Denver omelet with crisp hash browns and a side of regret you won’t actually regret because everything here is made from scratch and incredible. Just get there early because it fills up late in the morning and there's nothing worse than waiting with a splitting headache and the smell of homemade waffles hitting your nostrils.

Lunch

If your group insists on deep dish because “when in Rome,” Pequod’s in Lincoln Park is your one-and-only. Caramelized crust, sauce on top, the whole ceremony. Staff has an East Coast “we’re busy, what do you want?” edge, which is funny in the Midwest, and you won’t care once the pie hits the table. 

Lou Malnati’s is everywhere and a legit second choice. Want the OG storytime? Pizzeria Uno and Due in River North are tiny and make you put your order in 45 minutes before your butt hits the chair. Both have that old-school theater that’s worth it. And the buildings are as OG as it gets. Way better than the chain and a decent back up to the back up plan.

Not in the mood for a cheese casserole? Well then you're in luck becase Chicago’s real heritage is tavern-style. Vito & Nick’s on the far South Side is the pilgrimage. AKA the holy grail of cracker-thin, square-cut pizza. It’s a hike, but go anyway if you have the time and don't see yourself returning here anytime soon. 

Pizzamici in West Town is a reservation-only play for true tavern-heads. It's new but it's excellent. 

Near Sox Park, Phil’s is a perfect “we’re already down here” detour. Bungalow by Middle Brow in Logan Square gives you sourdough pies and brewery beers in one hit. 

Michael’s in Lakeview and D’Agostino’s near Wrigley are your pizza-and-pitcher lunch with actual bar vibes. 

Gallucci Pizzeria in Old Town and Spacca Napoli are both the real Neapolitan setup with a scene to match and as close as you'll get to real pizza in this city. 

If you're looking for East Coast style, you came to the wrong place. But the closest two that I've found here so far are Zaza's (a proud participant in Dave's One-Bite Pizza Fest), and Jimmy's Pizza Cafe- both located on the North Side and not too hard to get to.

If lunch for you is two sandwiches and an apology to your arteries, welcome. Portillo’s is arguably the most consistent menu in America, Italian beefs, dogs, char burgers, sausages, chopped salads, shakes, and that disrespectfully good chocolate cake. (Seriously, it;s crazy good.) 

JP Graziano’s in the West Loop is the king of Italian subs. Plan around hours (open till 4 p.m. Fri/Sat; closed Sun) or you’ll cry on the sidewalk. (Plus the bar/club next door/upstairs is the best)

Bari and D’Amato’s  both on Grand are right there with it, the Italian sub trinity. 

For South Side legend status, Ricobene’s and the breaded steak sandwich (a delicious brick). 

If you’ve got wheels, Johnny’s Beef in Elmwood Park is transcendent. Beef, roll, au jus, fries, Italian ice, even the hot dogs. Nothing else tastes like it. (Their italian ice is the closest thing I've had to Del's Lemonade outside of New England. IYKYK) Johnny’s Beef might be far, but it’s another pilgrimage worth making- trust me. 

Wings enthusiasts must hit Bird’s Nest, or Output Lounge (both also great bars). 

Day-Drinking Lunches That Turn Into “Shit, We Stayed Four Hours and Have A Dinner Reservation in 45 Minutes”

Big Star in Wicker Park might be the city’s patio Hall of Fame. Tacos that slap (as the kids say), pitchers of margaritas and whiskey sours, great-looking people, and a sunbeam that convinces you to order one more round three times. 

Parlor (West Loop & River North) is all-day patio party energy with pizza that does its job. Happy Camper (Old Town & Wrigley) is Parlor’s chaotic sibling with even nicer decor, and a top notch marketing program. Expect lots of hot chicks at each. 

Green Street Smoked Meats is top-tier Chicago BBQ in an alley fairyland. 

And yes, Au Cheval is still considered the best burger in America. But you have to do it right- arrive and put your name in, while expecting to wait 2-3 hours. No joke. Then go to next door to Lone Wolf next door or Haymarke Brewery t across the street, drink for a few hours, get the text, head bac and sit down. Order the double cheeseburger, split the fried bologna sandwich (sleeper showstopper), and share an order of fried chicken. Trust the process, and trust me on this. You;ll thank me later. 

The Gentleman Dinner- (Put on a Collar, Act Employed)

These boys weekends and hangouts with your guys in general get rarer as you get older. So make one night count. 

As you get older you stop getting opportunities to get all of your friends in one place. So value them while you have them. 

I think you should always do, at a minimum, one classy, more upscale dinner during a bachelor party weekend. Spend a few extra bucks. Treat the groom. Treat yourself. And don't let anybody bring down the vibes. Make it a night everybody laughs their ass off, enjoys a fantastic meal with some wine/drinks, and get some good group pics. You'll want it one day and wish you had one if you don't. 

The rest of the nights you can get more casual or laid back, but for the nights you're looking to do it right, you definitely came to the right city. 

Chicago is the steakhouse capital of the country. 

Facts are facts.

Sure, NYC has a few elite spots that are institutions. (Gallaghers, Keens, Striphouse) But the quality goes off a cliff from there. 

Chicago has not only elite-tier spots, but we have them by the handful. 

Bavette’s is the A++ if you can score a table. It's dark, jazzy, and has classy drinks that hit like a linebacker. Personally, I think it's the best steakhouse in the country. (New Yorkers will scoff, most not realizing that the hardest reservation to get in NYC- Four Charles Prime Rib is an offshoot little sister of Bavette's. Bavette’s is the steakhouse reservation everyone wants but no one can get (except Eddie somehow). It's got speakeasy lighting, perfect cuts, and old-school swagger. Absolutely perfect from top to bottom. 

Chicago Cut gives you our beautiful skyline through glass and big-baller service in a stunning dining room or seated outside right next to the river. Some of the best service and best meat you'll find in the country. (Their lobster-cargot is one of the best apps you'll find on the planet).

Maple & Ash is the “we made it” flex. Super expensive, lots of butter and salt on everything, but arguably the best "scene" and best looking crowd you'll find. Best espresso martini and one of the best wine listss in Chicago. Plus, if one of your buddies likes paying for sex, he'll be in heaven. (You can also call ahead and print something ridiculous on thge menu for the groom) (Their complimentary homemade waffle chips and onion dip + caviar is absolute CRACK)

Gibsons Italia does riverside decadence. One of the best views you'll find at any restaurant in the country. A straight shot view down the river right out into Lake Michigan. Same cuts yopu'll find at the original Gibson's, but with (in my opinion) an even better menu. And an Italian flair. (Best steak tartare in Chicago, also.)

RPM Steak is sleek, dialed, and consistent. 

Gene & Georgetti is the old-school time machine that still bangs. One of Frank Sinatra's favorite hangs and as old Chicago as it gets. 

Boeufhaus is the chef's steakhouse for cut nerds. They're not really downtown, out in Wicker Park, but they are an awesome spot with one of the best steak sandwiches you'll ever have. 

El Che does live-fire magic- group-pleaser and different. It's White Sox Dave's favorite steak house, and near the top of my list. Open fire grill they cook everything on, and unreal "party steak" that's perfect for a group, and the best carajillo you'll find in Chicago. 

Tango Sur is BYOB Argentinian heaven where you can get hammered in the waiting area and feast on a double filet with absolutely lethal chimichurri. This place is less fancy and pretentious than the others, but the food is incredible, and its BYOB so its basically a cheat code.

Tre Dita is the new-school, crypto-gains, “most beautiful room you stepped into” play- with a top cap that can end arguments. (No joke, their top cap might be the best non-Japanese steak I've ever had.) This place is stunning, and you need to be dressed up to fit in there. Wine list is incredible, service is impeccable, and it's expensive, but it will be one of the more memorable dinners you've ever had. You're also looking right out over Navy Pier and the lake at one of the most beautifuyl views you can find. Also, Evan Funke (ever heard of him?) is the Chef partner, and makes all the pastas from scratch. 

Speaking of Italian, Volare and La Scarola are loud, fun, and authentic. Volare is owned and operated by an actual Italian named Bennym who is straight off the boat from Sardegna. His head chef is from Rome (Mario), and half his staff are imports from southern Italy and Sicily. It's got the best pasta and sauces you'll find in the Midwest. (Their eggplant rotilini, pollo limone, and arrabiatta are the best I've had outside of Italy.)

La Scarola needs no introduction. We're always there, always talking about them on all the shows. It's where the infamous White Sox Dave wolfman picture took place and hangs on the wall. Their portions come out on dishes the size of the table and 

Viaggio is another where you will not have a bad dish and they make you feel at home. 

Elina’s is a hot, intimate spot that still nails the food. The two chefs who opened Carbone's kitchen with Mario in New York moved to Chicago and opened this spot. With all the greatest hits and some even better.

Bruna’s on the West Side is a throwback that feels like a time machine. 

Ignotz and Il Vicinato on the South Side are classics. 

Riccardo Trattoria in Lincoln Park is the real deal. 

Tufano’s is the kind of place your dad would call in a favor at and it never misses. 

Mart Anthony’s in West Loop is a sleeper you will be happy you found. 

Topo Gigio in Old Town is simple, cheap, and perfect for a bachelor group that wants to sit on a patio, crush bottles of wine without breaking the bank, and walk to bars on Wells after. 

Il Porcellino is solid for a big group and gets you close to everything else.

Monteverde is world-class but a little more refined, and Rose Mary is technically not Italian, its Croatian and Mediterranean, but the spirit is similar, and Joe Flamm is one of the best chefs in the country. I have been there more times than I can count and never had a miss. Book it early because it has been slammed for years.

Seafood? Joe’s Stone Crab. Everything else is just pretending. If you're gonna be that guy and insist on doing seafood in a midwestern state, you have to go to Joe’s Stone Crab. Where all their fish and crabs are imported daily from Miami.

PRO MOVE = For the wild cards, Trivoli Tavern is the HogSalt greatest hits house. If you can book it in advance, you can do the Au Cheval burger, the Bavette steak frites, pasta from Ciccio Mio, and everything that crew does best in one room. And it's modeled after a Wisconsin Supper Club. Elite ambiance. Massive cheat code. Just hard to get into like all of Hog Salt's places. So book way in advance. 

WHAT TO DO

Baseball

Chicago has two stadiums, offering two completely different experiences. One of the best parts about summer here is that you can watch baseball virtually every day. The schedules usually flip. If the Cubs are away, the White Sox are home, and vice versa. If you want the classic day baseball party, Wrigley is the move. You show up to Wrigleyville on game day and it feels like a theme park for adults.

Jonathan Daniel. Getty Images.

Grab a stack of bleacher seats, roll in twenty to thirty minutes before first pitch so you can grab beers, find seats near each other, and catch the anthem. Wrigley in the summer is packed with smokes who dress for the camera. If your buddy has a wandering eye, keep him on a leash. The in game vibe is perfect when the sun is out, and the post game bar hop turns into a second wave.

The neighborhood around Wrigley is not what it used to be. It got corporate. New real estate replaced legendary dives. There are still staples, but the feel changed. It is still a great day and still worth it, just do not get stuck there all night. 

You can day-drink your face off before the game in Wrigleyville, bounce between Murphy’s Bleachers, 

Old Crow, 

Sluggers (batting cages upstairs), HVAC, Country Club, 

Happy Camper, Moe's Cantina and not even realize the game’s started. The bleachers are a party, the atmosphere is unmatched, and post-game is just as wild as pre-game. 

Also, once you do step into Wrigley, its an experience unlike anywhere else in sports. Even Fenway. And the ballpark music is next level. Whoever set the tone there since they joined us in the 21st century and added speakers and video boards really did an incredible job. 

The post-game around Wrigley is one thing. But the late-night crowd that arrives for the scene, not the game, is not the crowd you want to hang with. Hit it hard and peel off to River North or West Loop after.

If you go South Side, the vibe is different in a good way. If it is a day game, the options are limited, which is part of the charm. 

The White Sox built a bar right next to the park where you can drink and walk straight into the stadium. It is convenient. If you want the neighborhood feel, walk a couple blocks to Turtles or Cork and Kerry. 

Save your appetite because the food inside is legitimately the best in baseball. That is the one thing Jerry Reinsdorf has nailed since he let Ozzie Guillen go. The hot dogs are next level, the other concessions are creative and excellent, and they somehow add new stuff every season instead of phoning it in.

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Sox Park doesn’t have the pre/post-game scene Wrigley does, but it’s got something Wrigley doesn’t: the best stadium food in baseball. Jerry Reinsdorf may have gutted the on-field product, but the concessions? Next level. No bullshit. Best in baseball. Even better than San Diego. 

Walk the entire concourse, sample everything, and thank me later. 

The ushers are the opposite of Wrigley. They are laid back and polite and you do not feel like you are getting frisked for trying to move two sections over. I prefer night games at Guaranteed Rate. The evenings play better in that ballpark. 

Like I said, pre-game at Cork & Kerry or Turtles, and check out the new bar right across from the park. And if you’re headed there, use it as an excuse to stop at Phil’s down the street for a sausage and giardiniera pizza on the way.

Boating & Day Drinking

Out of all the Great Lakes cities, Chicago has the biggest boating scene and it is not close. If the weather is nice, you will see thousands of boats on the lake. You can charter whatever fits the mood. Sailboats, yachts, pontoons, or jet skis, we have it. The day on the water is always a great day and nothing beats a long slow buzz under the sun. If you want to turn it up, the Playpen sits just north of Navy Pier. Boats drop anchor and tie up. Speakers go on blast. It turns into a floating block party. There is always a group of girls who regret committing to some sixty year old’s boat and are looking to hop to a better situation. If you want the river vibe, there are charters that will take your group through the downtown canyons and back out to the lake. You can rent private smaller yachts for just your group or buy into the larger boats like the Odyssey that include open bars and other groups. It is impossible to have a bad time if the sun is out.

But the real party is in the Playpen, a section just north of Navy Pier where boats tie up, music blares, and day-drinking rules the day. Bonus: there’s always a group of 20-somethings looking to escape the creepy old guy’s boat they mistakenly boarded.

Day Drinking

Day drinking is what this city does best. The second the first real spring day hits, everyone moves outside. Patios open, girls break out sundresses, and it feels like the city triples in size. You can pick a neighborhood and bar crawl for hours without hitting a dud. Wrigleyville is pure chaos during the day, especially when the Cubs are home. 

Old Town runs up and down Wells Street and has Benchmark, The Vig, Fireplace Inn, and a dozen more jammed together. 

River North mixes club energy with sports bar energy. Joy District has a rooftop that is a party by early afternoon and Parlay downstairs has so many televisions you can see three different games no matter where you are standing. 

There are old school dives tucked in between, like Snickers, Rossi’s, and Streeter’s, and if you head toward the Gold Coast, you get Pippin’s Tavern and the Viagra Triangle, where Gibsons, Tavern on Rush, and the new Bellevue draw a crowd that is equal parts power lunch and people watching. 

West Loop gives you that everyone here works in tech and still drinks like it is college vibe. Hit Texan Taco Bar for a country playlist and cheap beers, then cross Randolph to Bodega if you want the compact bottle service scene with a good DJ, and then find our spot Good Night John Boy on the corner of Peoria and Randolph. Look for the big disco ball or the JP Graziano’s sign we share a building with. It is a packed room that feels like a house party with a 70s disco soundtrack. The late-night burger and the pizza, (Done by Sexsons from Columbus- which Dave rated an 8.1) both sneak up on people because they are legitimately great. 

If disco is not your thing, there are a hundred other choices in a six block radius, from Federales for margaritas under the garage door to Haymarket Brewery, Lone Wolf, Green Street Smoked Meats, and Parlor.

Lincoln Park has the blend of college bar DNA and grown up money. Halligan and McGee’s near DePaul are still doing what they have always done. 

Wicker Park and Bucktown bring the indie and dive vibe with actual character. Louie’s Pub becomes a full-blown karaoke scene at night and Lottie’s is the neighborhood dive with the small patio that everyone ends up at anyway. 

Activities - Drinking Adjacent (WhirlyBall, Golf, Darts, Bowling, Karaoke & Breweries)

This isn’t just a bar city, it’s a day drinking with an activity city. Build a few anchor plays into the daylight hours and watch the entire weekend click. And trust me on some of these. 

WhirlyBall (Bucktown)-  Do not laugh this off. Before I moved here I had no idea what it was either. Then our Cubs Productions crew threw the holiday party there and it became the annual event nobody dares miss. Picture bumper cars plus lacrosse plus a basketball backboard you’re banking shots off, and then add pitchers between every game. The move is to book two courts and split into three or four teams, so one’s playing, one’s chirping, and two are drinking. Games are fast, rivalries form immediately, and by the third round your buddy who swore he’d “take it easy” is driving like he’s in Mad Max. Pro tip: WhirlyBall also has bowling, bocce, laser tag, pinball and arcades, with a full menu and cheap pitchers so you can stretch this into a three-hour daytime heater without trying.

Golf (private if you can, public if you can’t)- Chicago is quietly stacked. I could never get onto the private heavies on my own, but if you’ve got a connection, beg and bribe your way into Chicago Golf Club, Shoreacres, Butler National, Medinah #3, or Olympia Fields (North). That’s a bucket list stretch right there and a perfect bachelor flex if someone in the group has a member in his contacts. Public side is no consolation prize: Cog Hill #4 (Dubsdread) will test your soul, The Glen Club is a championship track that sets up perfectly for a group, Cantigny gives you 27 holes and a dialed operation, and Harborside (Port & Starboard) plus Jackson Park keep you right in the city so you can play, shower, and make dinner without sprinting.

Flight Club (River North)- Darts, but done like an actual night out. Real sisal boards, scoring handled automatically, leather couches, quick service, and cocktails that don’t taste like they were mixed in a mop sink. Book a semi‑private oche for two hours, run a round‑robin tournament, and let the trash talk do what it does.

Breweries you can make a day of - Goose Island put the city on the map; Revolution in Avondale is the largest independent in Illinois and Anti‑Hero is the house IPA of every softball team you’ll meet; Half Acre and Begyle are easy crowd‑pleasers; Haymarket in West Loop lets you post up before Au Cheval; and Middle Brow’s Bungalow in Logan pulls double duty with pizza that punches way above “brewery food.”

Bowling with a flair- Diversey River Bowl is the classic that’s always there when you need it, late or early. Southport Lanes brings old‑school Chicago charm and the right pace when the group needs two hours of friendly trash talk, cold beer, and fried food that won’t betray you.

Karaoke that turns into a scene- Louie’s Pub (Wicker Park) is my go‑to because by midnight, it flips from sing‑along to full spectacle. 

Mom’s Place downtown is the kind of place you “pop into for one song” and leave two hours later with a new best friend. 

Howl at the Moon scratches the dueling‑pianos itch and guarantees the whole bar knows the words. There's one in every city and they all fucking print money because it's a recipe that doesn't miss.

Night Life 

If your night leans country, Bub City downtown is the compact, loud, live music box that always punches above its size. Get there early because the line is real, the cover bands are elite, and the beers are cheap. 

Joe’s on Weed St. is the legendary venue where everyone from Luke Bryan to Garth Brooks has played. Check the schedule because their ticketed shows can sneak up on you. 

If you want the late night honky tonk, Carroll’s Pub up in Uptown runs to four in the morning and pours the cheapest beer in town with excellent burgers to keep you upright. Country Club in Wrigley and Old Crow on Clark pull double duty as pre and post game stops.

If you want blues, you're in the right city. Logan Square gives you the artsy bar and cocktail thing. If you want one pro move that is not obvious, hit California Clipper early in Logan so you can get a good table, 

then take your talents to Kingston Mines in Lincoln Park for late night blues. It is a killer two stop combo with two very different feels and you will thank me later.

Kingston Mines is the late-night machine that will keep you out until they turn the lights on. 

Buddy Guy’s Legends is a bucket list spot. Andy’s Jazz Club is the classic downtown set that works for a group that wants to actually listen.

If you want the club thing, River North is the circuit. TAO is the giant one everyone knows, the DJ calendar is heavy, and the bottle service show is the full parade. Joy District hits the club plus rooftop combo and tends to lean a little younger with a little more hip hop, with Parlay downstairs running as the sports bar with decent food and too many televisions. Tunnel, Electric Hotel, PRYSM, Underground, and Celeste round out a loop you can spin through without wasting the night in an Uber. Smartbar is the EDM purist spot upstairs from the Metro.

If you hate clubs but want to be out, Chicago is built for you. Richards and Snickers are the kind of dives that have not changed in thirty years and never should. Lottie’s in Bucktown is the neighborhood version people actually love. Louie’s turns into karaoke chaos. Flight Club lets you keep score while you drink properly and talk to people without screaming.

PRO MOVE = Check the music calendar for live music when you'll be here. We are such a great live music city. The Salt Shed, House of Blues, Metro, United Center, Concord, Radius, Thalia Hall, The Aragon, Chicago Theatre, any given weekend, at least one of these is hosting a band or artist or something worth your time.

Gambling in Chicago

Here’s the brutal truth: Chicago will have a massive Bally’s casino in River West eventually, but right now, the “temporary” version is a disaster. They took one of the most beautiful buildings in the city (The Medinah Temple) and turned it into a sad, smoky room full of absolute slimeballs posted outside 24/7. It’s everything you don’t want in your downtown. Thanks Lori and Brandon.

If you want actual casino fun, hit Rivers Casino in Des Plaines, minutes from O’Hare, with plenty of tables, restaurants, and action. Or take the shuttle to Horseshoe in Hammond, Indiana. There are also several other casinos just outside the city, and almost all run free shuttles to and from downtown.

Strip Clubs in Chicago

Chicago has one of the dumbest laws on the books. If a club serves alcohol, the dancers can not go fully nude. If the club is dry, they can. That means you are choosing between a beer and the full show. 

So plan accordingly. If you want close and easy and are fine with topless, Rick’s Cabaret is the downtown move. If you want the full show and are fine with a ride, Polekatz and Scores are the two best overall experiences. Admirals is an adventure. I will leave it at that. You go there when the goal is a story more than a polished night out. Take all of that for what it may be.

Conclusion - 

Vegas is the neon circus and Nashville is the bachelorette factory. They are exactly what they promise. But Chicago has range.

 You can watch a ballgame in the sun, have a steak dinner that feels like a scene from a mob movie, gamble, hit a strip club that has its own bizarre rule book, and finish on a rooftop, all inside a four-mile radius without ever feeling like you forced it. 

The food is better, the people are friendlier, the women are out in force when the weather turns, and every weekend has a festival you can stumble into. 

This city suffered through the winter and you can feel that in the summer. Everyone is trying to live as much as they can between May and September. That is the energy you want for a bachelor party.

The last thing I will say is this. Do not wing the whole weekend, and do not overplan it either. 

Pick your neighborhood home base. Book one nice dinner. Lock in your ballgame. Decide if you are a Playpen group or a Wrigley day drink group. Build in a breakfast or two that will save your life. Everything else will take care of itself. Chicago is built to fill in the blanks for you. And if you see me at Good Night John Boy, say what’s up. I will make sure your group is looked after and I might even buy the groom a shot if he survived whirleyball.